2-(4-Bromo­phen­yl)-3-(4-hy­droxy­phen­yl)-1,3-thia­zolidin-4-one

Vennila, J.P.; Thiruvadigal, D.J.; Kavitha, H.P.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536811025281

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1902

doi:10.1107/S1600536811025281

Open

access

2-(4-Bromophenyl)-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one

Jasmine P. Vennila,^a D. John Thiruvadigal,^b Helen P. Kavitha,^c G. Chakkaravarthi ^d ^* and V. Manivannan ^e

^aDepartment of Physics, Panimalar Institute of Technology, Chennai 602 103, India, ^bDepartment of Physics, SRM University, Kattankulathur Campus, Chennai, India, ^cDepartment of Chemistry, SRM University, Ramapuram Campus, Chennai 600 089, India, ^dDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: chakkaravarthi_2005@yahoo.com

(Received 25 June 2011; accepted 27 June 2011; online 6 July 2011)

In the title compound, C₁₅H₁₂BrNO₂S, the dihedral angle between the two aromatic rings is 87.81 (8)°. The five-membered thiazolidine ring has an envelope conformation, with the S atom displaced by 0.4545 (7) Å from the mean plane of the other four ring atoms. The crystal structure exhibits O—H⋯O, C—H⋯O, C—H⋯Br and C—H⋯ π interactions.

Related literature

For the biolgical activity of thiazolidine derivatives, see: Chen et al. (2000 ); Jacop & Kutty (2004 ); Kalia et al. (2007 ); Vicentini et al. (1998 ); Vigorita et al. (1992 ). For bond-length data see: Allen et al. (1987 ). For related structures, see: Akkurt et al. (2010 , 2011 ).

Experimental

Crystal data

C₁₅H₁₂BrNO₂S
M_r = 350.23
Orthorhombic, P b c a
a = 13.3367 (6) Å
b = 12.6292 (5) Å
c = 17.1230 (6) Å
V = 2884.1 (2) Å³
Z = 8
Mo Kα radiation
μ = 3.00 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.467, T_max = 0.586
18957 measured reflections
3617 independent reflections
2317 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.087
S = 1.02
3617 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C4–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	1.94	2.758 (2)	175
C5—H5⋯O2ⁱⁱ	0.93	2.53	3.361 (3)	149
C12—H12⋯Br1ⁱⁱⁱ	0.93	2.84	3.463 (2)	125
C15—H15⋯Cg2^iv	0.93	2.94	3.775 (2)	150
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025281/bt5562sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025281/bt5562Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025281/bt5562Isup3.cml

checkCIF report

Comment top

Thiazolidine derivatives exhibit herbicidal (Chen et al., 2000; Vicentini et al., 1998), antineoplastic (Vigorita et al., 1992), hypolipidemic (Jacop & Kutty, 2004) and anti-inflammatory (Kalia et al., 2007) activities. We report here the crystal structure of the titled compound (I) (Fig. 1).

In the title compound (I), the bond lengths in the molecule are normal (Allen et al., 1987) and in a good agreement with those reported previously (Akkurt et al., 2010,2011). The dihedral angle between the benzene rings (C4—C9) and (C10—C15) is 87.81 (8)°. The five-membered thiazolidine ring (N1/C2/C1/S1/C3) has an envelope conformation, with the S atom displaced by 0.4545 (7) Å from the mean plane of the four other ring atoms. In the molecule, the absolute configuration at atom C3 is R configuration. The crystal structure exhibit weak O—H···O, C—H···O, C—H···Br and C—H··· π (Fig. 2 and Table 1) interactions. Cg2 is the centroid of C4-C9 ring.

Related literature top

For the biolgical activity of thiazolidine derivatives, see: Chen et al. (2000); Jacop & Kutty (2004); Kalia et al. (2007); Vicentini et al. (1998); Vigorita et al. (1992). For bond-length data see: Allen et al. (1987). For related structures, see: Akkurt et al. (2010); Akkurt et al. (2011).

Experimental top

About 5 mmol of 4-[(4-Bromobenzylidene)-amino]-phenol was taken in a round bottomed flask. To this 25 ml of dry benzene and 10 ml of mercapto acetic acid was added. The content of the flask were refluxed on the water bath for 12 hrs, cooled and poured into water. The upper organic layer was washed successively with aqueous sodium bicarbonate and water and dried with anhydrous sodium sulfate. The solvent was removed by distillation under reduced pressure. The residue on recrystallization from ethanol several times, yielded diffraction quality crystals.Yield: 62%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis. H-bonds are shown as dashed lines; H atoms not involved in hydrogen bonding have been omitted.

2-(4-Bromophenyl)-3-(4-hydroxyphenyl)-1,3-thiazolidin-4-one top

Crystal data top

C₁₅H₁₂BrNO₂S	F(000) = 1408
M_r = 350.23	D_x = 1.613 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4654 reflections
a = 13.3367 (6) Å	θ = 2.4–23.8°
b = 12.6292 (5) Å	µ = 3.00 mm⁻¹
c = 17.1230 (6) Å	T = 295 K
V = 2884.1 (2) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	3617 independent reflections
Radiation source: fine-focus sealed tube	2317 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω and ϕ scans	θ_max = 28.4°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→16
T_min = 0.467, T_max = 0.586	k = −16→16
18957 measured reflections	l = −16→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0332P)² + 1.5996P] where P = (F_o² + 2F_c²)/3
3617 reflections	(Δ/σ)_max < 0.001
181 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₁₅H₁₂BrNO₂S	V = 2884.1 (2) Å³
M_r = 350.23	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.3367 (6) Å	µ = 3.00 mm⁻¹
b = 12.6292 (5) Å	T = 295 K
c = 17.1230 (6) Å	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII diffractometer	3617 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2317 reflections with I > 2σ(I)
T_min = 0.467, T_max = 0.586	R_int = 0.031
18957 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.087	H-atom parameters constrained
S = 1.02	Δρ_max = 0.45 e Å⁻³
3617 reflections	Δρ_min = −0.47 e Å⁻³
181 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.63473 (19)	0.1392 (2)	0.12609 (17)	0.0510 (7)
H1A	0.6916	0.1565	0.0932	0.061*
H1B	0.6280	0.0628	0.1279	0.061*
C2	0.54086 (16)	0.18813 (18)	0.09361 (15)	0.0344 (5)
C3	0.52231 (15)	0.23237 (19)	0.22967 (13)	0.0328 (5)
H3	0.5202	0.3035	0.2525	0.039*
C4	0.46182 (16)	0.15917 (18)	0.28031 (13)	0.0316 (5)
C5	0.41708 (17)	0.06902 (18)	0.25054 (14)	0.0342 (5)
H5	0.4201	0.0555	0.1972	0.041*
C6	0.36796 (18)	−0.00109 (19)	0.29911 (15)	0.0387 (6)
H6	0.3372	−0.0612	0.2788	0.046*
C7	0.36517 (19)	0.0191 (2)	0.37752 (15)	0.0427 (6)
C8	0.4075 (2)	0.1078 (2)	0.40845 (16)	0.0515 (7)
H8	0.4044	0.1204	0.4619	0.062*
C9	0.4548 (2)	0.1784 (2)	0.35973 (15)	0.0459 (7)
H9	0.4825	0.2399	0.3804	0.055*
C10	0.39180 (15)	0.28732 (16)	0.13260 (12)	0.0262 (5)
C11	0.31686 (16)	0.23068 (17)	0.09663 (13)	0.0305 (5)
H11	0.3274	0.1603	0.0830	0.037*
C12	0.22563 (16)	0.27854 (18)	0.08068 (13)	0.0324 (5)
H12	0.1745	0.2400	0.0571	0.039*
C13	0.21067 (15)	0.38358 (18)	0.09987 (13)	0.0313 (5)
C14	0.28555 (17)	0.43972 (18)	0.13648 (15)	0.0373 (6)
H14	0.2751	0.5101	0.1502	0.045*
C15	0.37581 (17)	0.39194 (18)	0.15282 (14)	0.0351 (5)
H15	0.4263	0.4301	0.1776	0.042*
N1	0.48688 (12)	0.23846 (14)	0.14893 (10)	0.0290 (4)
O1	0.51648 (12)	0.18202 (13)	0.02472 (10)	0.0432 (4)
O2	0.12206 (12)	0.43423 (13)	0.08407 (11)	0.0472 (5)
H2	0.0887	0.3982	0.0539	0.057*
S1	0.65353 (5)	0.19057 (6)	0.22246 (4)	0.04894 (19)
Br1	0.29816 (3)	−0.07918 (3)	0.44309 (2)	0.07795 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0342 (14)	0.0612 (17)	0.0575 (18)	0.0169 (13)	0.0023 (12)	0.0021 (14)
C2	0.0277 (12)	0.0379 (12)	0.0376 (16)	0.0002 (10)	0.0076 (11)	0.0026 (11)
C3	0.0271 (11)	0.0393 (12)	0.0320 (14)	0.0020 (10)	−0.0051 (10)	−0.0013 (10)
C4	0.0285 (11)	0.0418 (13)	0.0244 (13)	0.0066 (10)	−0.0036 (9)	−0.0008 (10)
C5	0.0393 (13)	0.0402 (12)	0.0229 (12)	0.0040 (11)	−0.0011 (10)	0.0000 (11)
C6	0.0402 (14)	0.0346 (13)	0.0413 (16)	0.0070 (11)	0.0006 (11)	0.0037 (11)
C7	0.0436 (14)	0.0497 (15)	0.0349 (16)	0.0170 (12)	0.0104 (12)	0.0136 (13)
C8	0.0581 (18)	0.0711 (19)	0.0254 (14)	0.0138 (15)	0.0042 (13)	−0.0003 (14)
C9	0.0483 (15)	0.0560 (16)	0.0335 (16)	0.0013 (13)	−0.0020 (12)	−0.0098 (13)
C10	0.0226 (10)	0.0330 (11)	0.0230 (12)	0.0013 (9)	0.0013 (9)	0.0011 (9)
C11	0.0320 (12)	0.0290 (11)	0.0305 (13)	0.0008 (10)	0.0002 (10)	−0.0040 (10)
C12	0.0258 (11)	0.0405 (13)	0.0310 (13)	−0.0017 (10)	−0.0041 (9)	−0.0098 (10)
C13	0.0253 (11)	0.0421 (12)	0.0265 (13)	0.0064 (10)	−0.0012 (9)	−0.0062 (10)
C14	0.0344 (13)	0.0331 (12)	0.0442 (15)	0.0038 (10)	−0.0071 (11)	−0.0118 (11)
C15	0.0264 (11)	0.0388 (13)	0.0400 (15)	−0.0039 (10)	−0.0059 (10)	−0.0062 (11)
N1	0.0234 (9)	0.0362 (10)	0.0273 (11)	0.0037 (8)	−0.0009 (8)	0.0024 (8)
O1	0.0371 (9)	0.0622 (11)	0.0304 (11)	0.0067 (8)	0.0078 (8)	−0.0037 (8)
O2	0.0324 (9)	0.0557 (11)	0.0534 (11)	0.0145 (8)	−0.0157 (8)	−0.0223 (9)
S1	0.0268 (3)	0.0699 (5)	0.0501 (5)	0.0060 (3)	−0.0060 (3)	0.0099 (4)
Br1	0.1055 (3)	0.0617 (2)	0.0667 (3)	0.02192 (19)	0.0415 (2)	0.03136 (17)

Geometric parameters (Å, º) top

C1—C2	1.503 (3)	C7—Br1	1.897 (2)
C1—S1	1.791 (3)	C8—C9	1.375 (4)
C1—H1A	0.9700	C8—H8	0.9300
C1—H1B	0.9700	C9—H9	0.9300
C2—O1	1.226 (3)	C10—C11	1.375 (3)
C2—N1	1.349 (3)	C10—C15	1.382 (3)
C3—N1	1.463 (3)	C10—N1	1.438 (3)
C3—C4	1.502 (3)	C11—C12	1.386 (3)
C3—S1	1.832 (2)	C11—H11	0.9300
C3—H3	0.9800	C12—C13	1.381 (3)
C4—C5	1.383 (3)	C12—H12	0.9300
C4—C9	1.385 (3)	C13—O2	1.371 (3)
C5—C6	1.380 (3)	C13—C14	1.376 (3)
C5—H5	0.9300	C14—C15	1.375 (3)
C6—C7	1.367 (3)	C14—H14	0.9300
C6—H6	0.9300	C15—H15	0.9300
C7—C8	1.361 (4)	O2—H2	0.8200

C2—C1—S1	107.98 (18)	C7—C8—H8	120.4
C2—C1—H1A	110.1	C9—C8—H8	120.4
S1—C1—H1A	110.1	C8—C9—C4	120.9 (2)
C2—C1—H1B	110.1	C8—C9—H9	119.6
S1—C1—H1B	110.1	C4—C9—H9	119.6
H1A—C1—H1B	108.4	C11—C10—C15	119.83 (19)
O1—C2—N1	124.3 (2)	C11—C10—N1	120.33 (19)
O1—C2—C1	123.5 (2)	C15—C10—N1	119.84 (19)
N1—C2—C1	112.2 (2)	C10—C11—C12	120.0 (2)
N1—C3—C4	113.86 (18)	C10—C11—H11	120.0
N1—C3—S1	105.06 (14)	C12—C11—H11	120.0
C4—C3—S1	111.99 (15)	C13—C12—C11	119.9 (2)
N1—C3—H3	108.6	C13—C12—H12	120.0
C4—C3—H3	108.6	C11—C12—H12	120.0
S1—C3—H3	108.6	O2—C13—C14	118.4 (2)
C5—C4—C9	118.5 (2)	O2—C13—C12	121.7 (2)
C5—C4—C3	121.7 (2)	C14—C13—C12	119.9 (2)
C9—C4—C3	119.7 (2)	C15—C14—C13	120.1 (2)
C6—C5—C4	120.7 (2)	C15—C14—H14	119.9
C6—C5—H5	119.6	C13—C14—H14	119.9
C4—C5—H5	119.6	C14—C15—C10	120.2 (2)
C7—C6—C5	119.0 (2)	C14—C15—H15	119.9
C7—C6—H6	120.5	C10—C15—H15	119.9
C5—C6—H6	120.5	C2—N1—C10	122.44 (18)
C8—C7—C6	121.6 (2)	C2—N1—C3	117.80 (18)
C8—C7—Br1	120.2 (2)	C10—N1—C3	119.42 (17)
C6—C7—Br1	118.2 (2)	C13—O2—H2	109.5
C7—C8—C9	119.2 (2)	C1—S1—C3	91.88 (11)

S1—C1—C2—O1	168.02 (19)	O2—C13—C14—C15	−179.5 (2)
S1—C1—C2—N1	−12.4 (3)	C12—C13—C14—C15	1.1 (4)
N1—C3—C4—C5	32.4 (3)	C13—C14—C15—C10	0.0 (4)
S1—C3—C4—C5	−86.6 (2)	C11—C10—C15—C14	−0.6 (3)
N1—C3—C4—C9	−151.3 (2)	N1—C10—C15—C14	179.1 (2)
S1—C3—C4—C9	89.7 (2)	O1—C2—N1—C10	2.4 (3)
C9—C4—C5—C6	−1.1 (3)	C1—C2—N1—C10	−177.1 (2)
C3—C4—C5—C6	175.3 (2)	O1—C2—N1—C3	175.7 (2)
C4—C5—C6—C7	−0.8 (3)	C1—C2—N1—C3	−3.9 (3)
C5—C6—C7—C8	1.6 (4)	C11—C10—N1—C2	52.6 (3)
C5—C6—C7—Br1	−179.47 (17)	C15—C10—N1—C2	−127.1 (2)
C6—C7—C8—C9	−0.5 (4)	C11—C10—N1—C3	−120.6 (2)
Br1—C7—C8—C9	−179.4 (2)	C15—C10—N1—C3	59.7 (3)
C7—C8—C9—C4	−1.5 (4)	C4—C3—N1—C2	−105.3 (2)
C5—C4—C9—C8	2.2 (4)	S1—C3—N1—C2	17.6 (2)
C3—C4—C9—C8	−174.2 (2)	C4—C3—N1—C10	68.2 (3)
C15—C10—C11—C12	0.1 (3)	S1—C3—N1—C10	−168.91 (15)
N1—C10—C11—C12	−179.6 (2)	C2—C1—S1—C3	18.91 (19)
C10—C11—C12—C13	1.0 (3)	N1—C3—S1—C1	−20.26 (17)
C11—C12—C13—O2	179.1 (2)	C4—C3—S1—C1	103.83 (18)
C11—C12—C13—C14	−1.6 (4)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.94	2.758 (2)	175
C5—H5···O2ⁱⁱ	0.93	2.53	3.361 (3)	149
C12—H12···Br1ⁱⁱⁱ	0.93	2.84	3.463 (2)	125
C15—H15···Cg2^iv	0.93	2.94	3.775 (2)	150

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, −y, z−1/2; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂BrNO₂S
M_r	350.23
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	13.3367 (6), 12.6292 (5), 17.1230 (6)
V (Å³)	2884.1 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	3.00
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.467, 0.586
No. of measured, independent and observed [I > 2σ(I)] reflections	18957, 3617, 2317
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.087, 1.02
No. of reflections	3617
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.47

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C4–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	1.94	2.758 (2)	175
C5—H5···O2ⁱⁱ	0.93	2.53	3.361 (3)	149
C12—H12···Br1ⁱⁱⁱ	0.93	2.84	3.463 (2)	125
C15—H15···Cg2^iv	0.93	2.94	3.775 (2)	150

Symmetry codes: (i) x−1/2, −y+1/2, −z; (ii) −x+1/2, y−1/2, z; (iii) −x+1/2, −y, z−1/2; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

The authors wish to acknowledge the SAIF, IIT, Madras, for the data collection.

References

Akkurt, M., Çelik, Í., Demir, H., Özkırımlı, S. & Büyükgüngör, O. (2010). Acta Cryst. E66, o1691–o1692. Web of Science CSD CrossRef IUCr Journals Google Scholar
Akkurt, M., Çelik, Í., Demir, H., Özkırımlı, S. & Büyükgüngör, O. (2011). Acta Cryst. E67, o914–o915. Web of Science CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chen, H. S., Li, Z. M. & Han, Y. F. (2000). J. Agric. Food Chem. 48, 5312–5315. Web of Science CrossRef PubMed CAS Google Scholar
Jacop, J. & Kutty, G. N. (2004). Indian Drugs, 41, 76–79. Google Scholar
Kalia, R., Rao, C. M. & Kutty, N. G. (2007). Arzneim. Forsch. (Drug Res.), 57, 616–622. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Vicentini, C. B., Manfrini, M., Veronese, A. C. & Guarneri, M. (1998). J. Heterocycl. Chem. 35, 29–36. CrossRef CAS Google Scholar
Vigorita, M. G., Basile, M., Zappala, C., Gabbrielli, G. & Pizzimenti, F. (1992). Farmaco, 47, 893–906. PubMed CAS Web of Science Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1902

doi:10.1107/S1600536811025281

Open

access